871210-26-3Relevant academic research and scientific papers
Practical synthesis of fluorous oxazolidinone chiral auxiliaries from α-amino acids
Hein, Jason E.,Geary, Laina M.,Jaworski, Ashley A.,Hultin, Philip G.
, p. 9940 - 9946 (2007/10/03)
A series of new fluorous-supported oxazolidinone chiral auxiliaries has been prepared using a versatile and general five-step pathway, starting from readily available chiral α-amino acids. The key feature of this synthesis is the efficient generation of a suitably active perfluoroalkyllithium species. By use of this protocol, the auxiliaries can be obtained in high enantiomeric purity and on multigram scales from L-phenylalanine and L-valine with overall yields as high as 55%. The new methodology also incorporates fluorous solid-phase extraction on the large scale, allowing bulk quantities (up to 25 g) of fluorous compounds to be purified from the crude reaction mixture.
